NPASS Compound

Structure

CID25848 OpenBabel06191715352D 36 40 0 0 1 0 0 0 0 0999 V2000 5.0694 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5103 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2245 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0225 0.6185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2245 -0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3796 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6898 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6898 2.9268 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9756 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5347 -0.4878 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.6898 0.9756 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5347 2.4390 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5347 -2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 1.4634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5347 1.4634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8449 -0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5347 -1.4634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9981 0.6185 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 -0.4878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 3.9024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 -2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 28 1 0 0 0 0 7 8 1 0 0 0 0 7 18 2 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 30 1 0 0 0 0 11 12 1 0 0 0 0 11 28 1 0 0 0 0 12 30 1 0 0 0 0 13 20 1 0 0 0 0 13 26 1 0 0 0 0 14 19 1 0 0 0 0 14 29 1 0 0 0 0 15 27 1 0 0 0 0 15 31 1 0 0 0 0 16 1 1 6 0 0 0 16 17 1 0 0 0 0 17 2 1 1 0 0 0 17 22 1 0 0 0 0 18 22 1 0 0 0 0 18 28 1 0 0 0 0 19 23 1 0 0 0 0 19 32 1 1 0 0 0 20 24 1 0 0 0 0 20 33 1 6 0 0 0 21 26 1 0 0 0 0 21 29 1 0 0 0 0 22 30 1 0 0 0 0 23 26 1 0 0 0 0 23 27 1 0 0 0 0 24 27 1 1 0 0 0 24 34 1 0 0 0 0 25 35 2 0 0 0 0 25 36 1 0 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 28 29 1 1 0 0 0 29 6 1 1 0 0 0 30 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	504.35
Volume:	532.122
LogP:	3.063
LogD:	2.065
LogS:	-3.878
# Rotatable Bonds:	2
TPSA:	118.22
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.363
Synthetic Accessibility Score:	5.238
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.762
MDCK Permeability:	9.01125622476684e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.036
30% Bioavailability (F30%):	0.187

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.164
Plasma Protein Binding (PPB):	94.08675384521484%
Volume Distribution (VD):	0.593
Pgp-substrate:	4.130692005157471%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.4
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.844
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.142
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.363
CYP3A4-substrate:	0.241

ADMET: Excretion

Clearance (CL):	2.009
Half-life (T1/2):	0.306

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.256
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.277
Maximum Recommended Daily Dose:	0.147
Skin Sensitization:	0.048
Carcinogencity:	0.041
Eye Corrosion:	0.005
Eye Irritation:	0.021
Respiratory Toxicity:	0.964

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC25848

Natural Product ID:	NPC25848
*Common Name:**	(1S,2R,4As,6As,6Br,8R,9R,10R,11R,12Ar)-8,10,11-Trihydroxy-9-(Hydroxymethyl)-1,2,6A,6B,9,12A-Hexamethyl-2,3,4,5,6,6A,7,8,8A,10,11,12,13,14B-Tetradecahydro-1H-Picene-4A-Carboxylic Acid
IUPAC Name:	(1S,2R,4aS,6aS,6bR,8R,9R,10R,11R,12aR)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Synonyms:
Standard InCHIKey:	PRAUVHZJPXOEIF-UQPQHHFRSA-N
Standard InCHI:	InChI=1S/C30H48O6/c1-16-9-10-30(25(35)36)12-11-28(5)18(22(30)17(16)2)7-8-21-26(3)13-20(33)24(34)27(4,15-31)23(26)19(32)14-29(21,28)6/h7,16-17,19-24,31-34H,8-15H2,1-6H3,(H,35,36)/t16-,17+,19-,20-,21?,22?,23?,24+,26-,27+,28-,29-,30+/m1/s1
SMILES:	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CCC4[C@@]5(C)C[C@H]([C@@H]([C@@](C)(CO)C5[C@@H](C[C@@]34C)O)O)O)C2[C@H]1C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL19097
PubChem CID:	12073158
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11816-015-0350-y]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17520525]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22966846]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Potency	4

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	35481.3	nM	PMID[459997]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	15848.9	nM	PMID[459997]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	5.0	nM	PMID[459997]
NPT791	Individual Protein	Cruzipain	Trypanosoma cruzi	Potency	=	22387.2	nM	PMID[459997]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC25848 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	1381
0.2-0.3	4664
0.3-0.4	11536
0.4-0.5	11180
0.5-0.6	5515
0.6-0.7	4980
0.7-0.8	2427
0.8-0.85	324
0.85-0.9	294
0.9-0.95	139
0.95-1	35

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC305464
1.0	High Similarity	NPC19376
1.0	High Similarity	NPC307282
0.9775	High Similarity	NPC32407
0.9775	High Similarity	NPC231063
0.9775	High Similarity	NPC145667
0.9775	High Similarity	NPC88116
0.9775	High Similarity	NPC263548
0.9775	High Similarity	NPC20235
0.9775	High Similarity	NPC282395
0.9775	High Similarity	NPC299996
0.967	High Similarity	NPC43686
0.957	High Similarity	NPC256247
0.956	High Similarity	NPC73004
0.956	High Similarity	NPC173744
0.956	High Similarity	NPC201657
0.956	High Similarity	NPC204961
0.9551	High Similarity	NPC71074
0.9551	High Similarity	NPC84319
0.9551	High Similarity	NPC52021
0.9551	High Similarity	NPC235884
0.9551	High Similarity	NPC300351
0.9551	High Similarity	NPC25299
0.9551	High Similarity	NPC472149
0.9551	High Similarity	NPC306541
0.9457	High Similarity	NPC106112
0.9457	High Similarity	NPC261935
0.9457	High Similarity	NPC247139
0.9457	High Similarity	NPC9613
0.9451	High Similarity	NPC32118
0.9451	High Similarity	NPC96916
0.9444	High Similarity	NPC307335
0.9444	High Similarity	NPC136313
0.9444	High Similarity	NPC275809
0.9444	High Similarity	NPC74855
0.9438	High Similarity	NPC49320
0.9438	High Similarity	NPC130278
0.9355	High Similarity	NPC271614
0.9355	High Similarity	NPC111214
0.9355	High Similarity	NPC29765
0.9348	High Similarity	NPC207922
0.9348	High Similarity	NPC476318
0.9348	High Similarity	NPC259733
0.9348	High Similarity	NPC158371
0.9348	High Similarity	NPC476327
0.9341	High Similarity	NPC159365
0.9333	High Similarity	NPC475708
0.9326	High Similarity	NPC127689
0.9326	High Similarity	NPC25906
0.9326	High Similarity	NPC234346
0.9326	High Similarity	NPC64872
0.9326	High Similarity	NPC290972
0.9326	High Similarity	NPC121798
0.9326	High Similarity	NPC263393
0.9326	High Similarity	NPC130520
0.9326	High Similarity	NPC59263
0.9326	High Similarity	NPC61543
0.9326	High Similarity	NPC225585
0.9326	High Similarity	NPC293048
0.9326	High Similarity	NPC270768
0.9255	High Similarity	NPC35239
0.9247	High Similarity	NPC255589
0.9247	High Similarity	NPC259788
0.9239	High Similarity	NPC473240
0.9239	High Similarity	NPC198245
0.9231	High Similarity	NPC133579
0.9231	High Similarity	NPC229281
0.9231	High Similarity	NPC474806
0.9222	High Similarity	NPC120968
0.9222	High Similarity	NPC126369
0.9222	High Similarity	NPC477872
0.9222	High Similarity	NPC7260
0.9222	High Similarity	NPC18872
0.9222	High Similarity	NPC227467
0.9222	High Similarity	NPC273621
0.9222	High Similarity	NPC470589
0.9222	High Similarity	NPC290614
0.9222	High Similarity	NPC111110
0.9222	High Similarity	NPC210037
0.9213	High Similarity	NPC52169
0.9213	High Similarity	NPC182797
0.9175	High Similarity	NPC477877
0.914	High Similarity	NPC230151
0.914	High Similarity	NPC88847
0.913	High Similarity	NPC188102
0.913	High Similarity	NPC114159
0.913	High Similarity	NPC87095
0.913	High Similarity	NPC191412
0.913	High Similarity	NPC6818
0.9121	High Similarity	NPC966
0.9121	High Similarity	NPC187722
0.9121	High Similarity	NPC324341
0.9121	High Similarity	NPC105189
0.9121	High Similarity	NPC282616
0.9121	High Similarity	NPC288833
0.9121	High Similarity	NPC228784
0.9121	High Similarity	NPC155120
0.9111	High Similarity	NPC274330
0.9111	High Similarity	NPC143232
0.9111	High Similarity	NPC198664
0.9101	High Similarity	NPC102683
0.9101	High Similarity	NPC88716
0.9101	High Similarity	NPC51700
0.9101	High Similarity	NPC130577
0.9101	High Similarity	NPC242468
0.9101	High Similarity	NPC18064
0.9101	High Similarity	NPC171203
0.9101	High Similarity	NPC98442
0.9101	High Similarity	NPC68160
0.9101	High Similarity	NPC293564
0.9101	High Similarity	NPC307426
0.9101	High Similarity	NPC142415
0.9053	High Similarity	NPC476195
0.9043	High Similarity	NPC189880
0.9043	High Similarity	NPC476878
0.9043	High Similarity	NPC203343
0.9043	High Similarity	NPC476879
0.9043	High Similarity	NPC312075
0.9032	High Similarity	NPC474727
0.9022	High Similarity	NPC158059
0.9022	High Similarity	NPC118490
0.9022	High Similarity	NPC86368
0.9022	High Similarity	NPC118519
0.9022	High Similarity	NPC202728
0.9011	High Similarity	NPC86372
0.9011	High Similarity	NPC172361
0.9011	High Similarity	NPC193750
0.9011	High Similarity	NPC291028
0.9	High Similarity	NPC473242
0.9	High Similarity	NPC290690
0.9	High Similarity	NPC246708
0.9	High Similarity	NPC40552
0.9	High Similarity	NPC474512
0.9	High Similarity	NPC181225
0.9	High Similarity	NPC470629
0.9	High Similarity	NPC17733
0.8989	High Similarity	NPC72638
0.8958	High Similarity	NPC118964
0.8958	High Similarity	NPC54909
0.8958	High Similarity	NPC476132
0.8958	High Similarity	NPC233012
0.8947	High Similarity	NPC260149
0.8947	High Similarity	NPC188833
0.8947	High Similarity	NPC58942
0.8936	High Similarity	NPC132824
0.8936	High Similarity	NPC116457
0.8925	High Similarity	NPC296164
0.8925	High Similarity	NPC222047
0.8925	High Similarity	NPC277399
0.8913	High Similarity	NPC471588
0.8913	High Similarity	NPC158030
0.8913	High Similarity	NPC6255
0.8913	High Similarity	NPC38754
0.8913	High Similarity	NPC233455
0.8913	High Similarity	NPC65120
0.8913	High Similarity	NPC4036
0.8913	High Similarity	NPC474525
0.8913	High Similarity	NPC145067
0.8901	High Similarity	NPC470588
0.8901	High Similarity	NPC95246
0.8901	High Similarity	NPC474972
0.8901	High Similarity	NPC161751
0.8878	High Similarity	NPC475036
0.883	High Similarity	NPC148523
0.883	High Similarity	NPC139570
0.883	High Similarity	NPC83693
0.8817	High Similarity	NPC214756
0.8817	High Similarity	NPC295643
0.8817	High Similarity	NPC272075
0.8817	High Similarity	NPC291373
0.8817	High Similarity	NPC298554
0.8812	High Similarity	NPC108709
0.8812	High Similarity	NPC75747
0.8812	High Similarity	NPC7870
0.8812	High Similarity	NPC199457
0.8812	High Similarity	NPC102914
0.8812	High Similarity	NPC68419
0.8812	High Similarity	NPC110139
0.8804	High Similarity	NPC46441
0.8804	High Similarity	NPC474728
0.8804	High Similarity	NPC120840
0.8804	High Similarity	NPC113989
0.8788	High Similarity	NPC80566
0.8778	High Similarity	NPC237344
0.8778	High Similarity	NPC213412
0.875	High Similarity	NPC174663
0.875	High Similarity	NPC477876
0.875	High Similarity	NPC477875
0.875	High Similarity	NPC164349
0.8737	High Similarity	NPC473158
0.8737	High Similarity	NPC98874
0.8737	High Similarity	NPC327179
0.8737	High Similarity	NPC157113
0.8737	High Similarity	NPC62516
0.8725	High Similarity	NPC179434
0.8723	High Similarity	NPC91010
0.8723	High Similarity	NPC209868
0.8723	High Similarity	NPC78580
0.8723	High Similarity	NPC80365
0.8723	High Similarity	NPC23621

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC25848 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	1756
0.2-0.3	3801
0.3-0.4	2220
0.4-0.5	715
0.5-0.6	221
0.6-0.7	192
0.7-0.8	40
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8913	High Similarity	NPD7515	Phase 2
0.8526	High Similarity	NPD7748	Approved
0.8454	Intermediate Similarity	NPD7902	Approved
0.8144	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD7900	Approved
0.8065	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7645	Phase 2
0.7755	Intermediate Similarity	NPD8035	Phase 2
0.7755	Intermediate Similarity	NPD8034	Phase 2
0.7719	Intermediate Similarity	NPD8328	Phase 3
0.7677	Intermediate Similarity	NPD6399	Phase 3
0.7658	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7638	Approved
0.7604	Intermediate Similarity	NPD3618	Phase 1
0.7579	Intermediate Similarity	NPD4786	Approved
0.7573	Intermediate Similarity	NPD7640	Approved
0.7573	Intermediate Similarity	NPD7639	Approved
0.7553	Intermediate Similarity	NPD3667	Approved
0.7551	Intermediate Similarity	NPD5328	Approved
0.7547	Intermediate Similarity	NPD5739	Approved
0.7547	Intermediate Similarity	NPD6675	Approved
0.7547	Intermediate Similarity	NPD6402	Approved
0.7547	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD6412	Phase 2
0.7407	Intermediate Similarity	NPD6899	Approved
0.7407	Intermediate Similarity	NPD7320	Approved
0.7407	Intermediate Similarity	NPD6881	Approved
0.74	Intermediate Similarity	NPD6079	Approved
0.7387	Intermediate Similarity	NPD4632	Approved
0.7379	Intermediate Similarity	NPD4755	Approved
0.7374	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7525	Registered
0.7339	Intermediate Similarity	NPD6373	Approved
0.7339	Intermediate Similarity	NPD6372	Approved
0.7327	Intermediate Similarity	NPD4202	Approved
0.7315	Intermediate Similarity	NPD5697	Approved
0.7315	Intermediate Similarity	NPD5701	Approved
0.7312	Intermediate Similarity	NPD6118	Approved
0.7312	Intermediate Similarity	NPD6115	Approved
0.7312	Intermediate Similarity	NPD6697	Approved
0.7312	Intermediate Similarity	NPD6114	Approved
0.7297	Intermediate Similarity	NPD8297	Approved
0.7273	Intermediate Similarity	NPD7102	Approved
0.7273	Intermediate Similarity	NPD6883	Approved
0.7273	Intermediate Similarity	NPD4634	Approved
0.7273	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7290	Approved
0.7248	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6686	Approved
0.7238	Intermediate Similarity	NPD4696	Approved
0.7238	Intermediate Similarity	NPD5285	Approved
0.7238	Intermediate Similarity	NPD5286	Approved
0.7238	Intermediate Similarity	NPD4700	Approved
0.7232	Intermediate Similarity	NPD8133	Approved
0.7228	Intermediate Similarity	NPD6411	Approved
0.7216	Intermediate Similarity	NPD3665	Phase 1
0.7216	Intermediate Similarity	NPD3666	Approved
0.7216	Intermediate Similarity	NPD3133	Approved
0.7212	Intermediate Similarity	NPD6083	Phase 2
0.7212	Intermediate Similarity	NPD6084	Phase 2
0.7207	Intermediate Similarity	NPD8130	Phase 1
0.7207	Intermediate Similarity	NPD6649	Approved
0.7207	Intermediate Similarity	NPD6847	Approved
0.7207	Intermediate Similarity	NPD6617	Approved
0.7207	Intermediate Similarity	NPD6869	Approved
0.7207	Intermediate Similarity	NPD6650	Approved
0.7204	Intermediate Similarity	NPD6116	Phase 1
0.7193	Intermediate Similarity	NPD7115	Discovery
0.7182	Intermediate Similarity	NPD6013	Approved
0.7182	Intermediate Similarity	NPD6012	Approved
0.7182	Intermediate Similarity	NPD6014	Approved
0.7155	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD6882	Approved
0.7143	Intermediate Similarity	NPD7507	Approved
0.7117	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5222	Approved
0.7115	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5221	Approved
0.7115	Intermediate Similarity	NPD4697	Phase 3
0.7103	Intermediate Similarity	NPD5226	Approved
0.7103	Intermediate Similarity	NPD5211	Phase 2
0.7103	Intermediate Similarity	NPD5225	Approved
0.7103	Intermediate Similarity	NPD5224	Approved
0.7103	Intermediate Similarity	NPD4633	Approved
0.7097	Intermediate Similarity	NPD6117	Approved
0.7091	Intermediate Similarity	NPD6011	Approved
0.7071	Intermediate Similarity	NPD7146	Approved
0.7071	Intermediate Similarity	NPD6409	Approved
0.7071	Intermediate Similarity	NPD6684	Approved
0.7071	Intermediate Similarity	NPD5330	Approved
0.7071	Intermediate Similarity	NPD7521	Approved
0.7071	Intermediate Similarity	NPD7334	Approved
0.7054	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5173	Approved
0.7043	Intermediate Similarity	NPD6009	Approved
0.7041	Intermediate Similarity	NPD3668	Phase 3
0.7037	Intermediate Similarity	NPD5175	Approved
0.7037	Intermediate Similarity	NPD5174	Approved
0.703	Intermediate Similarity	NPD6101	Approved
0.703	Intermediate Similarity	NPD4753	Phase 2
0.703	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7736	Approved
0.7009	Intermediate Similarity	NPD5223	Approved
0.7	Intermediate Similarity	NPD3573	Approved
0.699	Remote Similarity	NPD5779	Approved
0.699	Remote Similarity	NPD5778	Approved
0.6981	Remote Similarity	NPD4225	Approved
0.6972	Remote Similarity	NPD5141	Approved
0.6967	Remote Similarity	NPD7319	Approved
0.6952	Remote Similarity	NPD7614	Phase 1
0.6944	Remote Similarity	NPD7632	Discontinued
0.6931	Remote Similarity	NPD6672	Approved
0.6931	Remote Similarity	NPD6903	Approved
0.6931	Remote Similarity	NPD5737	Approved
0.6923	Remote Similarity	NPD7516	Approved
0.6917	Remote Similarity	NPD7492	Approved
0.6909	Remote Similarity	NPD4767	Approved
0.6909	Remote Similarity	NPD6008	Approved
0.6909	Remote Similarity	NPD4768	Approved
0.6882	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD4754	Approved
0.6864	Remote Similarity	NPD6054	Approved
0.6864	Remote Similarity	NPD8294	Approved
0.6864	Remote Similarity	NPD8377	Approved
0.6864	Remote Similarity	NPD6059	Approved
0.686	Remote Similarity	NPD6616	Approved
0.6857	Remote Similarity	NPD5695	Phase 3
0.6847	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7328	Approved
0.6838	Remote Similarity	NPD7327	Approved
0.6833	Remote Similarity	NPD7604	Phase 2
0.6822	Remote Similarity	NPD5696	Approved
0.681	Remote Similarity	NPD6274	Approved
0.6809	Remote Similarity	NPD7339	Approved
0.6809	Remote Similarity	NPD6942	Approved
0.6807	Remote Similarity	NPD8379	Approved
0.6807	Remote Similarity	NPD5983	Phase 2
0.6807	Remote Similarity	NPD8296	Approved
0.6807	Remote Similarity	NPD8335	Approved
0.6807	Remote Similarity	NPD8033	Approved
0.6807	Remote Similarity	NPD8380	Approved
0.6807	Remote Similarity	NPD8378	Approved
0.6804	Remote Similarity	NPD4695	Discontinued
0.6803	Remote Similarity	NPD8293	Discontinued
0.6803	Remote Similarity	NPD7078	Approved
0.6786	Remote Similarity	NPD4730	Approved
0.6786	Remote Similarity	NPD4729	Approved
0.6786	Remote Similarity	NPD5128	Approved
0.678	Remote Similarity	NPD7101	Approved
0.678	Remote Similarity	NPD7100	Approved
0.675	Remote Similarity	NPD6370	Approved
0.6737	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5279	Phase 3
0.6731	Remote Similarity	NPD5281	Approved
0.6731	Remote Similarity	NPD5284	Approved
0.6721	Remote Similarity	NPD6336	Discontinued
0.6698	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5210	Approved
0.6698	Remote Similarity	NPD4629	Approved
0.6695	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD5250	Approved
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD5249	Phase 3
0.6667	Remote Similarity	NPD6015	Approved
0.6667	Remote Similarity	NPD6909	Approved
0.6636	Remote Similarity	NPD7732	Phase 3
0.6635	Remote Similarity	NPD6698	Approved
0.6635	Remote Similarity	NPD46	Approved
0.6634	Remote Similarity	NPD5329	Approved
0.6632	Remote Similarity	NPD3703	Phase 2
0.6612	Remote Similarity	NPD5988	Approved
0.661	Remote Similarity	NPD6317	Approved
0.6609	Remote Similarity	NPD5215	Approved
0.6609	Remote Similarity	NPD5217	Approved
0.6609	Remote Similarity	NPD5216	Approved
0.66	Remote Similarity	NPD4788	Approved
0.6571	Remote Similarity	NPD7637	Suspended
0.6569	Remote Similarity	NPD6098	Approved
0.6557	Remote Similarity	NPD6067	Discontinued
0.6555	Remote Similarity	NPD6313	Approved
0.6555	Remote Similarity	NPD6314	Approved
0.6545	Remote Similarity	NPD5344	Discontinued
0.6538	Remote Similarity	NPD6904	Approved
0.6538	Remote Similarity	NPD6673	Approved
0.6538	Remote Similarity	NPD6080	Approved
0.6535	Remote Similarity	NPD4197	Approved
0.6529	Remote Similarity	NPD8513	Phase 3
0.6529	Remote Similarity	NPD6921	Approved
0.6529	Remote Similarity	NPD8517	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data